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Method for preparing 4-octyl itaconate by enzymatic selective catalysis

A technology for preparing monooctyl itaconic acid and catalysis is applied in the fields of biochemical industry and enzyme catalysis, and can solve the problems of high separation cost, low conversion rate of monoester, many by-products, etc., and achieves high product purity, easy separation, The effect of high conversion rates

Active Publication Date: 2020-06-23
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, the synthesis of itaconic acid monoester either uses high-cost itaconic acid anhydride as a substrate, or there are many by-products, the conversion rate of monoester is not high, and the subsequent separation cost is relatively high

Method used

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  • Method for preparing 4-octyl itaconate by enzymatic selective catalysis
  • Method for preparing 4-octyl itaconate by enzymatic selective catalysis
  • Method for preparing 4-octyl itaconate by enzymatic selective catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] Example 1: Preparation of 4-monoctyl itaconate under normal pressure in a solvent system.

[0096] Step 1. Under normal pressure conditions (1.013×10 5 pa), with 1g itaconic acid (7.69mmol) and 10g (76.9mmol) n-octanol as raw materials, add 0.5g Novozym435 lipase (10000U / g), add solvent toluene 12mL (toluene:n-octanol=1: 1 volume ratio), at 50 DEG C, carry out esterification reaction 24h in 200rpm shaker reactor; The conversion rate of itaconic acid determined by gas chromatography is 99%, and the productive rate of 4-monoctyl itaconate is 98% (see attached image 3 );

[0097] Step 2. After the esterification reaction, remove the lipase by filtering through a solvent filter (0.45 μm nylon filter membrane), pour the reaction solution into a separatory funnel and add saturated saline according to the volume ratio of the reaction solution to saturated saline at 1:1 (Concentration is about 35%), fully mix and shake, let stand for 6h, remove the lower aqueous phase, and c...

Embodiment 2

[0100] Example 2: Preparation of 4-monoctyl itaconate under reduced pressure in a solvent system.

[0101] Step 1. under reduced pressure (1000pa), in there-necked flask, drop into 1g itaconic acid (7.69mmol) and 10g (76.9mmol) n-octanol as raw material, add 0.5g Novozym435 lipase (10000U / g), Add 12 mL of solvent toluene (toluene:n-octanol=1:1 volume ratio), control the water bath at 40°C, and carry out the esterification reaction in a shaker reactor at 200 rpm, connect it to a glass water separator, and carry out the esterification reaction for 12 hours; gas chromatography The conversion rate of itaconic acid was determined to be 99%, and the yield of 4-monoctyl itaconate was 97%;

[0102] Step 2. After the esterification reaction, remove the lipase by filtering through a solvent filter (0.45 μm nylon filter membrane), pour the reaction solution into a separatory funnel and add saturated saline according to the volume ratio of the reaction solution to saturated saline at 1:1 ...

Embodiment 3

[0105] Example 3: Under the solvent system, the packed bed reactor continuously prepared 4-monoctyl itaconate.

[0106] Step 1. Under normal pressure conditions (1.013×10 5 pa), with 5g itaconic acid (7.69mmol) and 50g (76.9mmol) n-octanol as raw materials, add solvent toluene 60mL (toluene:n-octanol=1:1 volume ratio) and mix well, as the reaction substrate;

[0107] Step 2. in long 20cm, inner diameter 1cm, in the steel jacket packed bed reactor of outer diameter 2cm, fill in 2.5g Novozym435 lipase (10000U / g), glass beads are filled in at both ends, by plunger pump The material was pumped into the packed bed reactor from bottom to top, the flow rate was 0.4mL / min, and the jacket temperature was controlled by a circulating water bath at 30°C. When the residence time is 10min; the conversion rate of itaconic acid is 51% as determined by gas chromatography, and the output of 4-monoctyl itaconic acid is 50%; The yield of monooctyl acid was 94%. The total reaction time for all ...

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Abstract

The invention discloses a method for preparing 4-octyl itaconate by enzymatic selective catalysis, and belongs to the fields of biochemical engineering and enzyme catalysis. According to the method, lipase is used as a catalyst, itaconic acid and n-octanol are used as raw materials, and the 4-octyl itaconate is synthesized by selective catalysis under a solvent system or a solvent-free system. Themethod provided by the invention uses the lipase as the catalyst, so that the method has advantages of mild conditions, simple separation, strong specificity, high catalytic efficiency, short reaction time, multiple reuse batches, etc. Compared with other catalysts, the lipase used in the invention has advantages of greenness, safety, environmental friendliness, etc., and the 4-octyl itaconate obtained by catalysis is one of emerging small-molecular anti-inflammatory substances.

Description

technical field [0001] The invention belongs to the fields of biochemical industry and enzyme catalysis. Specifically, it relates to a method for preparing 4-monooctyl itaconate by enzymatic selective catalysis. [0002] technical background [0003] Itaconic acid is a dicarboxylic acid containing a C=C unsaturated double bond, which has important applications in the fields of chemical industry, polymer materials and medicine. In recent years, itaconic acid, as a small molecule anti-inflammatory drug, has attracted much attention in treating chronic inflammation, reducing Zika virus infection, and regulating metabolic pathways in vivo (Hooftman&O'Neill.Trends in immunology.2019, 40(8), 687- 698). Itaconic acid can be combined with the cysteine ​​residue of key enzymes in the metabolic pathway through Michael addition reaction to achieve alkylation, and then play a regulatory role, such as the activation of the alkylation reaction with the 151-position cysteine ​​residue of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/64C12P7/6454C12P7/6436
CPCC12P7/6436C12P7/6454C12Y301/01007
Inventor 邓利刘昌升王亦琳刘佳豪王芳
Owner BEIJING UNIV OF CHEM TECH
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